WELCOME TO A CONVERSATION about “Letters to a Young Entrepreneur”

In Letters to a Young Entrepreneur, I share some of the highlights of my entrepreneurial journey. On this website, I continue to offer reflections on my leadership experiences, and very much welcome your comments, critique and suggestions. Most importantly, I invite you to share your own experiences and insights, as well.

My hope is that through this dialogue we will all benefit from our common entrepreneurial adventure, and perhaps provide some new approaches to the challenges we all face as we embody our dreams.

MUST WE BE MUSK-ESQUE TO SUCCEED IN BREAKOUT ENTERPRISES? An entrepreneur’s reflections on Elon Musk’s creativity, capability and character

On December 2, 2011 I posted an article titled “The Steve Jobs Paradox.” (1) It was prompted by the passing of Jobs, an event that touched me profoundly and motivated me to read Walter Isaacson’s Jobs biography, which appeared shortly after Steve’s death.

I am now moved to write about another legendary Silicon Valley entrepreneur who is still alive and thriving: Elon Musk. I became particularly interested in Musk because my grandson, Brent Schroeter, a junior in Computer Science and Engineering at the University of Washington, was taking a quarter off to intern at SpaceX. Since he first began his studies at UW, Brent had been involved with another Musk initiative, the Hyperloop Project. His decision to apply for an internship at SpaceX obviously signaled that he has been quite enthralled by his Hyperloop work and wanted to explore another Musk initiative more deeply. When I mentioned this to a friend, he suggested I read the 2015 book by Ashlee Vance, Elon Musk: Tesla, SpaceX, and the Quest for a Fantastic Future. (2)

I draw eight primary inferences common to both the Musk story as told by Vance and the Jobs story as told by Isaacson:

  1. Every entrepreneurial venture needs at least one individual who is absolutely consumed by a vision. That vision needs to be injected into others, who then catch the fire.
  2. The “injected” fire has the potential to completely engulf doubt. I have proposed in the past that one of the most vital roles of the entrepreneurial leader is to absorb uncertainty (3). Engulfing doubt is one path for doing so.
  3. I use the word “engulf” here judiciously; I did not say “consume”. There has to be enough room for different opinions and disagreement. It seems that Musk allows a limited amount of disagreement, but not much. Not clear how much Jobs did. This puts an enormous onus on the intellectual brilliance of the entrepreneur, something most of us do not have. Is this cult-of-personality sustainable? Scalable?
  4. The entrepreneurial leader needs to strike a difficult balance between transparency and the absorption of uncertainty. I am not sure that either Musk or Jobs accomplished this balance. Their transparency seems limited, yet their endeavors succeed. What does that teach us?
  5. I have long espoused that one of the important characteristics of an entrepreneurial leader is empathic capability, a key component of generating trust within the organization. Musk does not seem to have this empathic quality, yet he seems to be succeeding so far. What does this tell us?
  6. Musk and Jobs both have ground-breaking visions. This is coupled with a style that borders on despotic. Is it necessary to have a despotic edge to succeed in a vision as grand as placing a man on Mars?
  7. Musk and Jobs display an incredible capacity to envision the future and are reported to have a remarkable intellect. Are both ingredients necessary in one individual to accomplish extraordinary entrepreneurial achievements? Can this capacity be a shared characteristic among several people? How?
  8. Finally, both Jobs and Musk evidence an incredible eye for consumer-friendly style in their products: the iPhone and the Tesla. What is it in their own single-minded drive and their intellectual brilliance that enables such remarkable products? What can we learn from this?

This is not the first time I have been touched by Musk. I have witnessed and shared the anticipation of several friends who had patiently awaited delivery of the Tesla Model X, and their enthusiasm when they finally received their cars. And I have been awestruck at the successes of SpaceX launches. Watching the launch of Falcon Heavy on February 6th was, for me, one of the highlights of recent times — especially seeing those two booster rockets return to earth, deploy their legs at the last minute, and land effortlessly.

As I read Vance’s book, many thoughts swirled in my head. At times, I was maddened by Musk’s bizarre and impulsive behavior (spinning out and causing major damage to his million-dollar McLaren F1 sports car, for example). At other times, I was floored by his genius. And I often found myself pondering what Musk’s story told me about entrepreneurship and leadership. It has made me re-examine some of the characteristics that I hold dear in the entrepreneur and form the basis for my book and my teaching.

Perhaps what drew me most to Musk was his uniqueness in the Silicon Valley of today. The overwhelming majority of enterprises born and incubated in this valley over the past few decades have been software oriented — a world characterized by dramatic rises and falls, incredible turnover, and astounding advances possible only in a field fostering the testing of new ideas and their implementation at “warp speed.” Along comes an individual who started in that churning virtual environment and decides to embark on a very different entrepreneurial journey which I am much more familiar with: creating and manufacturing tangible products that require extensive science and engineering, must be produced to very strict quality standards, and have product life cycles measured in decades, not months. This is the entrepreneurial world in which I grew up in and made my minor mark, so it speaks to me.

One aspect particularly intrigues me (or better yet “bothers” me) as I think about what I learn from the Jobs and Musk stories. In many of my writings I place great importance in trust as the KEY ingredient for success in entrepreneurship as well as fulfillment in life. I believe when trust is absent or breaks down, it severely threatens all of our endeavors. Clearly, I only have a limited vantage point into the deeper inside stories of either the Jobs or Musk ventures. Yet on the surface I fail to see the trust element – except as it involves the overwhelming and dominating intellect of both Steve Jobs and Elon Musk, and, in the case of Musk, his financial power. I examine the trust question further below.

Here are some of the references and passages in Vance’s book that stood out for me, and some reflections on what they teach me:

  • Musk seems to be able to engulf doubt through two conditions: his total personal financial commitment and his incredible intellectual mastery of all aspects of his ventures. He proves this mastery by stepping in when his employees question the reasonableness of the goals he imposes. As relayed in Vance’s book:

…the absolute worst thing that someone can do is inform Musk that what he’s asking is impossible. An employee could be telling Musk that there’s no way to get the cost on something like that actuator down to where he wants it or that there is simply not enough time to build a part by Musk’s deadline. “Elon will say, ‘Fine. You’re off the project, and I am now the CEO of the project. I will do your job and be CEO of two companies at the same time. I will deliver it,’” Brogan [Kevin Brogan, one of the early engineers at SpaceX] said. “What’s crazy is that Elon actually does it. Every time he’s fired someone and taken their job, he’s delivered on whatever the project was. (4)

  • Most of us mortals cannot match the combination of business acumen and intellectual capability of Musk. So, for those of us in the “normal” range, what does this suggest? A possibility: If overwhelming intellect and financial dominance is necessary to succeed in monumental visions, it becomes even more important for us regular mortals to live and work in a trust environment since we depend so much more on the intellect and character of those we attract to join us in the adventure rather than just our own super-capabilities. The key is to make sure that these strengths exist among our senior executives and that they are harnessed as if they were one actor. For we need a common purpose and shared values, and deep mutual trust.
  • From the Vance book, I get the impression that Musk shows very little regard for the impact of his decisions and actions on his employees. His visionary fire seems so all consuming that it totally inhibits him from extending his sensitivities to the individual. His business goals, whether micro or macro, dominate his thinking and his actions. His employees seem to be merely his means to an end rather than fully vested co-journeyers.  I have always argued that an important characteristic of a good leader is the empathic capability to relate to his/her colleagues. It is not clear from the book whether Musk has that quality. This then raises a key question: To what extent, when we tackle enormously ambitious and groundbreaking dreams, must we have a hardness of execution that does not allow for empathy? Perhaps to invent and implement a new drug manufacturing technology or a pollution free gas turbine (my old worlds) you can be – and may have to be – empathic, but to shoot for Mars you cannot afford such softness.
  • I have also argued that transparency is a key element in building a resilient team and overcoming the hurdles we inevitably face when growing a company. This is another component of the trust equation. Musk seems to concentrate his “transparency” on one edict: If you are with me you do what I ask, even if you think the request is unreasonable; if you do not agree, “here is the door.” Does this allow for enough doubt to explore alternatives, advance knowledge, and prevent major errors? When I sought my grandson’s impression, he commented, “According to those I have talked with who work directly with Elon, the answer is ‘Yes’ — Musk always welcomes dissenting voices if and only if they are backed by rigorous evidence.”
  • I would argue that in the early creative process such rigorous evidence is rarely available, and the exploratory nature of breakthrough science requires openess to the ideas of others even in their formative stage. That is the secret of discovery, as so well expressed by Albert Szent-Gyorgyi, the Hungarian biochemist recipient of the 1937 Nobel Prize in Physiologyand Medicine: “Discovery consists of looking at the same thing as everyone else and seeing something different.”
  • I pointed out earlier that Musk’s enterprises are different from the typical Silicon Valley companies’ in that his products take years to develop. Thus, the fast trial-and-error possible with software startups is not realistic. However, it seems that the intense, high-speed culture Musk has imposed on his enterprises does breed a spirit of fast trials and quick abandonment of ideas that do not show promise. The rapid timetable and cost-reduction demands in Musk’s playbook foster quick assessment of possibilities. As Vance writes, “Rarely did Tesla get hung up over analyzing a situation. The company would pick a plan of attack, and when it failed at something, it failed fast and tried a new approach.”(5)  We can all learn from this mindset. I will remember the “it failed fast and tried a new approach” description.
  • There seems to be another consequence of Musk’s intense and single-minded focus on the grand goal: He seems to quickly put past failures in context of the larger aim, rather than dwelling on them. This is actually remarkable in an individual who reportedly reacts so harshly to disagreement and failure. It indicates to me a remarkable, multiplex personality, which, when it counts, is able to acknowledge challenges even if they suggest imperfection in the design or execution. And more importantly, while he seems to be quick to criticize employees who do not toe the Musk line or flow with the Musk expectation, he is able to put setbacks in perspective for his teams and picks them back up when we more ordinary leaders might have been overwhelmed. That is suggested in Vance’s description of the failure of the first SpaceX launch in September 2008:

The failed launch left many SpaceX employees shattered. “It was so profound seeing the energy shift over the room in the course of thirty seconds,” said Dolly Singh, a recruiter at SpaceX. “It was like the worst fucking day ever. You don’t usually see grown-ups weeping, but there they were. We were tired and broken emotionally.” Musk addressed the workers right away and encouraged them to get back to work. “He said, ‘Look. We are going to do this. It’s going to be okay. Don’t freak out,’” Singh recalled. “It was like magic. Everyone chilled out immediately and started to focus on figuring out what just happened and how to fix it. It went from despair to hope and focus.”(6)

  • While Musk is the face of his companies, I get the impression that one key to his survival are a few colleagues who provide the approachable bridge between his hard and often uncaring demeanor and his employees. This seems to be the case at SpaceX, as embodied by Gwynne Shotwell. Recruited as the seventh employee, she is described in the Vance book as the “interpreter” of Musk’s edicts, the softener and smoother of the rough spots, and the reinforcer of the culture that Musk has imprinted. She is now President of SpaceX. To succeed, Gwynne has had to park her own ego at the company door. As Vance puts it: “Shotwell has been a consistent presence at SpaceX almost since day one, pushing the company forward and suppressing her ego to ensure that Musk gets all the attention he desires.”(7)
  • When I talked with my grandson about Shotwell, he commented, “I agree completely. Gwynne’s business and engineering instincts would make her an invaluable asset to any organization, and her emotional poise is so perfectly matched to Elon’s style that when one steps back, it is hard to imagine SpaceX enjoying its success today without her.”

The BIG question: Should we teach our students to be like Musk or Jobs?

My preliminary answer is, “Yes, but… not totally.” There are many elements in the Musk story that offer very important lessons for making us better entrepreneurs and better leaders. A total Musk is going to be rare. Not many of us have the prodigious brilliance of Musk’s mind, his ability to absorb and understand facts in so many fields, and his practically photographic memory. However, I contend that even if we did, Musk-ness needs to be tempered by a greater humanity and, in the end, such a combination would be more effective and powerful for the companies we are building.

Some of the other elements we should emulate are well-summarized at the end of Vance’s book:

Page [Larry Page, the founder of Google and a friend of Musk] holds Musk up as a model he wishes others would emulate — a figure that should be replicated during a time in which the businessmen and politicians have fixated on short-term, inconsequential goals. “I don’t think we’re doing a good job as a society deciding what things are really important to do,” Page said. “I think like we’re just not educating people in this kind of general way. You should have a pretty broad engineering and scientific background. You should have some leadership training and a bit of MBA training or knowledge of how to run things, organize stuff, and raise money. I don’t think most people are doing that, and it’s a big problem. Engineers are usually trained in a very fixed area. When you’re able to think about all of these disciplines together, you kind of think differently and can dream of much crazier things and how they might work. I think that’s really an important thing for the world. That’s how we make progress.”(8)

As I re-read my 2011 Jobs post, I am struck by how many of my points there also apply to the Musk story, as told by Vance. There is much for us to learn from both of these remarkable individuals, and, in Musk’s case, this is a continuing story.


1. https://ricardolevy.com/2011/12/02/the-steve-jobs-paradox/

2. Ashlee Vance Elon Musk, Tesla, SpaceX and the Quest for a Fantastic Future (EPub Edition MAY 2015)

3. Ricardo Levy Letters to a Young Entrepreneur: Succeeding in Business Without losing at Life (San Francisco, Catalytic Publishers, 2015) Chapter 7

4. Vance, Elon Musk, Tesla, SpaceX and the Quest for a Fantastic Future, EPub Edition page 240 of 392

5. Vance, Elon Musk, Tesla, SpaceX and the Quest for a Fantastic Future, EPub Edition page 84 of 392

6. Vance, Elon Musk, Tesla, SpaceX and the Quest for a Fantastic Future, EPub Edition page 57 of 392

(7) Vance, Elon Musk, Tesla, SpaceX and the Quest for a Fantastic Future, EPub Edition page 146 of 392

(8) Vance, Elon Musk, Tesla, SpaceX and the Quest for a Fantastic Future, EPub Edition page 152 of 392


Dear Reader:

My last two posts dealt with how to navigate through complexity. I detailed one approach that has worked for me, but it is by no means the only approach. We each need to discover our own path. What has helped me find my path, and I believe may also help you, is the practice of meditation.

I am frequently asked by friends and students how to meditate. Despite many years of practice, I still feel thoroughly unprepared to answer this question. Since I was first exposed to meditation, I have leaned on my teachers. In the 70s and 80s, I looked to the wonderful author and Transactional Analysis pioneer, Dorothy Jongeward. More recently, my dear friend and mentor, Andre Delbecq, was my stalwart guide and, for five years, it was to him that I turned to teach the session on meditation and spirituality in my Stanford entrepreneurship class. Andre’s class was a favorite of my students, and one of the most impactful of all our sessions. Unfortunately, two weeks before he was to teach the Fall 2016 class, Andre passed away at age 80. Since I had recorded his lecture from the previous year, I decided to play it for my class, rather than attempting to recreate it. It was my tribute to him. His words touched me as if I was hearing them for the first time. His spirit permeated the lecture hall, and many students commented afterwards how deeply he touched them. Several have followed up and, when I see them, they tell me they are continuing to meditate.

Now that I no longer have Andre to lean on, I am struggling to find a way to help students with the practice of meditation. It has, for so many years, been a key in my ability to cope with increasing responsibilities and an increasingly complex business. Looking at my sources, I have re-discovered two books that speak directly to the topic from two different traditions and approaches. Both books have the same title: How to Meditate. One, by Eknath Easwaran, comes from the Hindu tradition; the other, by Pema Chödrön, stems from the Buddhist tradition:

Eknath Easwaran, How to Meditate (Tomales, CA: Nilgiri Press, 2016)
Pema Chödrön, How to Meditate (Boulder, CO: Sounds True, 2013)

You may have noticed that I have quoted both authors in my past posts. I do not presume to describe here what these special authors teach. Their own words speak so eloquently that I would be robbing you of the experience to savor them for yourselves. Instead, I will share with you some excerpts so that you can taste the beauty of these little books, then perhaps you will be inspired to pick them up and read them. I assure you that once you do, you will be hooked.

What is so marvelous about both of these short treasures is that they are each written as an intimate and personal call from the author to enter the practice of meditation as a way to be more completely present in our lives. I could almost say that both of these authors are pleading with us. Eknath’s first chapter is titled “Invitation to a Journey.” He starts by relaying the story of Humphrey, the whale that captivated so many of us when he got lost in the San Francisco Bay in 1985. Humphrey was ultimately “invited” to find the way out, back to his deep-water world. Eknath describes Humphrey’s apparent impulse, when he finally sensed that he was in the open sea:

Then, free to go wherever he chose, he must instead have felt a silent command: “North. Go north. Go home.” No details, no map, no companions, no guide, just a direction and a desire in response to an overriding imperative from within: go home. It is very much like that on the journey of meditation too. Once you turn inward, the words of the passages urge you forward in response to a summons from the very depths of the heart. This need to return to the source of our being is nothing less than an evolutionary imperative – the drive to realize our full human potential.

Pema subtitled her book “A Practical Guide to Making Friends with Your Mind.” In her introduction she says:

…meditation is about a compassionate openness and the ability to be with oneself and one’s situation through all kinds of experiences. In meditation, you’re open to whatever life presents you with. It’s about touching the earth and coming back to being right here. While some kinds of meditation are more about achieving special states and somehow transcending or rising above the difficulties of life, the kind of meditation that I’ve trained in and that I am teaching here is about awakening fully to our life. It’s about opening the heart and mind to the difficulties and the joys of life — just as it is. And the fruits of this kind of meditation are boundless.

One of Pema’s recurring themes in many of her books is a reminder that thoughts are the creations of our minds. They can lead to physical consequences resulting from stress, anger or fear, which are very real to us. We often forget that these began as creations of our minds, as mere thoughts. Our challenge is not to allow them to become 100% of our reality. Pema constantly urges us to stop before this 100%, and go beneath to uncover the source of the thought, the source of the emotion. Meditation is a path to reach “beneath.” According to Pema, to do so we need to be fully in the present moment:

The present moment is the generative fire of our meditation. It is what propels us toward transformation. In other words, the present moment is the fuel for your personal journey. Meditation helps you to meet your edge; it’s where you actually come up against it and you start to lose it. Meeting the unknown of the moment allows you to live your life and to enter your relationships and commitments ever more fully. This is living wholeheartedly.

For both Pema and Eknath, meditation is a transformative process. What I find so valuable is that, from my vantage point, they arrive at the same end point but come from two quite different approaches. Eknath’s practice, which he calls “Passage Meditation,” emphasizes using a memorized passage as a means to go into a very deep quiet zone, reaching a state that disconnects from the sounds, thoughts, sensations, emotions and distractions that are continuously accosting us. Pema, in contrast, emphasizes being fully present in whatever state we are in at the moment, regardless of the emotions that may be gripping us; to be fully present amidst any pains, stresses, desires, anxieties or joys. She then guides us to go beneath these sensations so we can “see” beyond them and start to understand them and deal with them. For her, these emotions and sensations are the teachers of the transformation:

We turn our emotions into frozen objects and invest them with truth, and as a result they have so much power over us. So we train again and again in coming back to the object of meditation as a way of interrupting that fixated quality. The grasping and fixation — that’s really what we’re interrupting.

Pema speaks of emotions as being energy that we can harness. She quotes a passage from “The Myth of Freedom and the Way of Meditation” by her teacher, Chögyam Trungpa Rinpoche:

So the intelligent way of working with emotions is to try to relate with their basic substance. The basic “isness” quality of the emotions, the fundamental nature of the emotions, is just energy. And if one is able to relate with the energy, then the energies have no conflict with you. They become a natural process.

In my own practice, I use both approaches: sometimes employing a passage to enter the deep space (following Eknath’s advice, I often use the wonderful St. Francis Prayer that I’ve reproduced at the end of this post); and sometimes, rather than go deep, I go wide, staying with my immediate state of being and my emotions. Both approaches move me, both touch me, and both teach me. For me, meditation is a continually evolving process: I do not pre-plan which mode I will engage. I allow myself to be taken in either direction. In the end, they both become my guides to the same place of appreciation and gratitude. They both help me be more fully in the present. Most importantly, I attempt to follow the “edict” that both emphasize: Meditate every day.


To make progress in meditation, you must be regular in your practice of it… There is only one failure in meditation: the failure to meditate faithfully. A Hindu proverb says, “Miss one morning, and you need seven to make it up.” Or as Saint John of the Cross expressed it, “He who interrupts the course of his spiritual exercises and prayer is like a man who allows a bird to escape from his hand; he can hardly catch it again” … Put your meditation first and everything else second; you will find, for one thing, that it enriches everything else. Even if you are on a jet or in a sickbed, don’t let that come in the way of your practice. If you are harassed by personal anxieties, it is all the more important to have your meditation; it will release the resources you need to solve the problems at hand.


Meditation is a transformative process, rather than a magic makeover in which we doggedly aim to change something about ourselves. The more we practice, the more we open, and the more we develop courage in our life. In meditation you never really feel that you “did it” or that you’ve “arrived.” You feel that you just relaxed enough to experience what’s always been within you. I sometimes call this transformative process “grace.” Because when we’re developing this courage, in which we allow the range of our emotions to occur, we can be struck with moments of insight, insights that could never have come from trying to figure out conceptually what’s wrong with us, or what’s wrong with the world. These moments of insight come from the act of sitting in meditation, which takes courage, a courage that grows with time.

So, dear Reader, go and get these little books. And perhaps they will help answer your question about what meditation is all about and why some of us are so hooked on it.

Your friend,


The Prayer of St Francis:

Lord, make me an instrument of thy peace.
Where there is hatred, let me sow love;
Where there is injury, pardon;
Where there is doubt, faith;
Where there is despair, hope;
Where there is darkness, light;
Where there is sadness, joy.

O divine Master, grant that I may not so much seek
To be consoled as to console,
To be understood as to understand,
To be loved as to love;
For it is in giving that we receive;
It is in pardoning that we are pardoned;
It is in dying to self that we are born to eternal life.

And if you want a lighter passage, which I sometimes also use in my meditation, here is a wonderful poem by Mary Oliver: Why I Wake Early:

Hello, sun in my face.
Hello, you who make the morning
and spread it over the fields
and into the faces of the tulips
and the nodding morning glories,
and into the windows of, even, the
miserable and crotchety –

best preacher that ever was,
dear star, that just happens
to be where you are in the universe
to keep us from ever-darkness,
to ease us with warm touching,
to hold us in the great hands of light –
good morning, good morning, good morning,

Watch, now, how I start the day
in happiness, in kindness.

To which I usually add: “…and in gratitude.


My last post was the basis for a workshop I conducted at the International Association of Management, Spirituality and Religion Conference at the University of Arkansas on May 19, 2017. The intense discussions during and after the workshop have led me to further thoughts on the very important question of how we can unlock our leadership capacity. While my concept of transforming the crucible to a chalice clearly resonated with the participants, the personal experiences that were shared in the session shows that each of us develops our own way to cope with complexity.

As I faced challenges during my entrepreneurial career, I managed even without analyzing the mechanics of how I did so. Somehow, I made it through, long before I understood my chalice path to clarity. As I will relay at the end of this note, I survived more by intuition than by deliberate process. Today, the concept of a “crucible of complexity” and the path to the other side, as described by Oliver Wendell Holmes, resonates with me and I can see elements of it even in earlier ordeals. Being aware of the necessary process now makes it much more likely that I will employ it consciously in the future. I hope that by sharing it, my understanding will help others navigate complex situations and perhaps reach better decisions.

A number of inherent conditions come with the passage through complexity, regardless of whether we avail ourselves of the crucible-to-chalice metaphor:

    1. Gaining clarity “on the other side” does not, in itself, represent leadership. It is only insight. But this insight affords us a unique opportunity to lead. Yet only if we choose to act on this clarity can we capture the “leadership moment.” We do so the moment we lend voice to this insight.

    2. In that instant, if the moment is right and our insight is on point, we are expressing the thoughts that are latent in the minds of all the participants: When we lend voice to our clarity we are helping the group recognize a path to resolution of the complexity.

    3. We have an opportunity to lead, yet we are also undertaking an obligation to the others with whom we “resonate.” They put their trust in us. This results in an understanding that is unwritten: A covenant that we will do our best to carry through. It is critical that we be aware of this covenant if we are to be good leaders.

    4. While the ability to capture the “essence” of the group in the leadership moment is crucial, we should not rely on it alone. We need to have the discipline to check in with all team members to make sure there is also common clarity in understanding the path forward. I have often failed in this because, in the pressures of the moment and the dynamics of action, I have assumed too much.

    5. The ability to lead does not necessarily require hierarchy: As long as there is an understanding of leadership and followership and a collective team goal, any member of the team can become the de-facto leader for that endeavor. If that happens within an already established leadership context, so much the better; if not, it is an opportunity for new leaders to emerge.

    6. I emphasize followership because I find that we spend a lot of time on leadership development and training and not enough time on its counterpart, followership development and training.

    7. The “leadership link” between leader and followers is strengthened by the leader’s willingness to be vulnerable: To accept shortcomings and fears. It creates in the leader a greater capacity to be fully in the moment and allows a true connection. If the situation is of real import, and the clarity we articulate comes from that deep “point vierge” described by Thomas Merton in the wonderful passage I quoted in my previous post, we do well to expose this deep place. It opens the corresponding deep place in others in the group, thus enhancing the strength of the mutual commitment. It also creates a “safe space” for more intimate dialogue and a strong bonding. It has the potential to create unbeatable teams.

    8. Willingness to be vulnerable is not only important for good communication between the team and us: It is important to our own inner growth. This is especially necessary when we are facing failures. The times when I have been willing to admit vulnerability to myself have enabled me to traverse difficult situations better and have led to profound personal growth. To accomplish this, I have had to own my experiences, especially my failures. They have become my most real teachers.

    9. Admission of these failures has also increased the chances that others on my team would step in and supplement my shortcomings, thus increasing our odds for success.

    10. Being open to our own shortcomings and being forthcoming with our vulnerability are also important ways for us to teach others. To the extent that one’s voice comes from that deep “point vierge,” it will engage the listening and receiving capacity of others more intensely. This is true both for teammates in a leadership situation and for students in a learning situation.

I mentioned that the crucible-to-chalice metaphor is only one way to “see the way.” In essence, it permits us to view the path through complexity as a sacred task rather than a burden. It enables us to better cope with the unknown.

As I said at the outset, I have had many difficult and complex situations in my career without the benefit of the crucible-chalice perspective, and somehow I did know the path. I relayed one such situation, which occurred in 1990, at the opening of my Arkansas workshop. One of our major investors and partners abruptly withdrew from the relationship with our company and plunged us into the worse crisis of our fifteen years in business. With the cancellation of their contract, we lost much of the funding for several key technical programs and faced the need for dramatic actions to survive. One of those actions was to lay off 25% of our staff of 85 scientists and engineers, most of whom I had personally attracted to join our company with the inducement that I had wanted them to share our dream of building a unique scientific and engineering discovery organization. It was the worst moment in my entrepreneurial experience, truly the “dark night of my soul”, to borrow a very apt term from the catholic tradition (1).

At the workshop, I asked the participants to take a few moments and reflect on events in their professional or personal lives that they would similarly consider as dark nights of their souls. I did not mean for these moments to be public, I just wanted them to use these personal experiences to engage more deeply in the topic. Nevertheless many did share, and this enormously enriched our subsequent conversation. It made very real to the group the transformative step that I described in my previous post as my way to cope with the sort of complexity that threatens to freeze our ability to think and act. I used a graphic to convey my concept of the transformation of crucible to chalice:


This visual conjured a better image than my words to convey the transformation that had, in effect, enabled me in 1990 to survive that dark night, find simplicity on the other side of complexity, and lead the company forward. I had “intuitively” converted a burden into a sacred task, and driven by our team’s common goal, that revelation eventually enabled us to not only recover, but to blossom.

As several of the workshop participants relayed their own experiences, we considered them in the context of the crucible of anxiety and the need to overcome the resulting inner forces. When we examined the hurdles that can prevent us from gaining clarity on the other side and acting on this clarity, a list emerged:

  • Fear of failure
  • Fear of embarrassment
  • Fear of the unknown
  • Too anchored in the current perspective
  • Too shocked by the dark night
  • Inability to expand our horizons
  • Lack of trust in ourselves, in others
  • Resistance to change
  • Lack of preparation
  • Lack of acceptance of the knowing that comes with full immersion in change

These are the barriers that block the path forward!

I ask you to reflect on the following questions:

  1. Think back to your own experiences of the “dark night of the soul.” How did you cope?
  2. Does the crucible-to-chalice metaphor help you gain clarity on your predicament?
  3. Have you experienced moments when you have seen clarity but have held back from voicing it? Do any of the hurdles in the list above apply?
  4. What have you learned about yourself from these experiences? Can you make them into your best teachers?
  5. Can you clear away your own barriers?

In my last post, I wrote about the role of meditation in helping me with these questions. Recently, I ran across a passage from one of my favorite authors, Pema Chödrön, in her book How to Meditate. She suggests that all we need to do to clear our path is get out of our own way:

    “In meditation, you learn how to get out of your own way long enough for there to be room for your own wisdom to manifest, and this happens because you’re not repressing this wisdom any longer. When we learn how to relax into the present moment, we learn how to relax with the unknown.”


(1) For an explanation of the term “Dark Night of the Soul” see Eckhart Tolle, or you can go to the source: The Dark Night of the Soul by St John of the Cross.

Dealing With Uncertainty: From the Crucible of Anxiety to the Chalice of Change — LESSONS IN LEADERSHIP

Dear Reader:

Last year I published two posts dealing with uncertainty. I have continued to reflect on the events that prompted the posts. I want to share with you some further insights into the challenge of handling complexity at times of crisis, and in particular what they tell me about leadership. My contemplation helped me uncover additional aspects about the leadership capacity within us, and stimulated a continuing search for what makes good leadership and how to develop it. It also made me realize how little I know, and how much help I need to better understand this topic. It has led me to recast my previous posts and focus on the question of teaching ourselves – and others – to be better leaders.

I will be using this article as the basis for a workshop I am leading on May 19, 2017 at the International Association of Management, Spirituality and Religion Conference at the University of Arkansas. The essence of my theme at that workshop is how to discover and unlock the leadership capacity inside all of us.

I very much seek and welcome any ideas, critique, suggestions and insights that you may have on this important topic.

First, a reminder: What makes us entrepreneurs is our consuming drive to bring new products to market to fulfill perceived needs. What makes us entrepreneurial leaders is our capacity to embrace the unknown and guide our organizations in times of difficulty and uncertainty. To be in the midst of this action, either as a driver or contributor, has been my joy for many years, and this joy continues as I serve on Boards and teach. The most difficult element then and now, as I dwell in uncertainty, is to find the right time and best way to act, so as to help shift uncertain situations toward greater clarity and positive resolution. I have come to recognize that nothing helps sharpen one’s capacity as much as living through a difficult experience.

A Situation that Challenged Me — Both Professionally and Personally

One of the companies for which I served as a Board member had reached an impasse. We were making substantial progress in a breakthrough healthcare technology, and were the first to engage in clinical trials. Some of our most recent results were awe inspiring. Yet we were frustrated by the financial market forces making it difficult to continue to finance development of the much-needed medical breakthroughs we were targeting. At the Board’s request, the CEO was asked to consider alternatives. The options were disconcerting: narrowing the research focus; reducing expenses, with consequent layoffs; realigning the ranks of executives to better correspond to a down-sized operation; mounting one more aggressive effort to attract financial resources in a very hostile fund-raising environment. The CEO’s recommendation was to double-down on the most advanced project and discontinue all others, which would significantly reduce the company’s expenses. The focus was to be driven by the COO, who had helped develop the options and was running the R&D. It was a sound recommendation that the Board accepted.

This recommendation was not unexpected, and is certainly not unusual in entrepreneurial ventures as they pioneer new technology. I had faced these same choices in the companies I had founded and grown. So I thought that with my long experience as an entrepreneur, I was well equipped to handle these complex issues as a Board member. As it turns out, I did have the right intuition about what to do, but in retrospect, I failed in several aspects of the execution. And this is where my learning begins.

The selected scenario required a realignment of the executive ranks to better correspond to a down-sized operation. The CEO counseled a measured approach. The Board felt that action needed to be taken immediately, which necessitated a drastically slimmed-down organization from top to bottom. In the course of the deliberations, I saw a clear – and to me obvious – path to reconcile the CEO’s desire for a measured transition and the Board’s sense that immediate drastic action was needed: Ask the CEO to become Chair of the Board and promote the COO to the top executive position. Not rocket science. But the sense of urgency in the moment and the severity of the timeline did not give much breathing room for the “of course” considerations that so often come only in retrospect. To me, “my” solution had all the correct ingredients: It would signal a smooth transition to the outside world; it would allow for a harmonious transfer of power and realignment while implementing the difficult step of reducing and focusing the organization. There was, for me, one more factor, which on the one hand, compounded my personal thought process, and on the other, opened up potential pathways to help resolve the crisis. The CEO had become a personal and very close friend of mine, and he trusted me. Unraveling and appreciating this additional personal pressure on me was to come later. At the time, I simply “knew” what had to be done.

The Board decided to implement the immediate change. They agreed to my suggested approach regarding the CEO. Because of my close personal relationship with the CEO, I volunteered to join the Board Chair in conveying the decision. I just could not do otherwise, unpleasant as the news would be that the Board wanted to accelerate something the CEO thought should be done in a more systematic manner. I was feeling the emotions that everyone was experiencing and, in particular, anticipating the CEO’s likely emotional dilemma. I was not about to leave this tough job to someone else.

The subsequent series of one-to-one meetings with the CEO and the COO – who had to agree to take over immediately from the person who had hired him in the first place – are hard to describe or even for me to revisit. I would not wish this experience on anyone. And here is the hardest part of the story (as if the rest was not hard enough): To my disappointment, in the end the Board and the CEO could not agree on the steps forward, in spite of my recommendation to put in place the smooth executive transition that I had envisioned. The CEO left the company. I had failed, and this weighed heavily on me.

In retrospect, I was obviously not fully aware of the enormity of the inner forces that were acting on me as I participated in these intense deliberations. I could intimately feel the disappointment of the scientists and physicians who had tirelessly dedicated a significant portion of their lives and careers to driving this important, next-generation technology forward. I could intimately feel the struggle of my friend, the CEO who had staked his life on pursuing the goals of this company in which he deeply believed and to which he had dedicated over fifteen years of his life. I also sensed the forces acting on the other Board members as they wrestled to make the best decision possible under very unpleasant circumstances and a tightening timeline.

To make matters even worse, shortly after we took these streamlining and tightening actions and the CEO had left, we received reports from our clinical trials that while the impact of our treatment was still significant, the level of progress of our study patients had slowed — something we could not immediately explain and had never before observed. We could see ways to determine the cause and implement adjustments, but in our current financial circumstances this was impossible. On top of the trauma of the staff reductions inherent in narrowing the operation’s focus and of the change in leadership, our team was now faced with clinical results that would significantly extend the timeline to commercial implementation and render the company’s survival much more perilous.

A Message of Significance

These events led to many sleepless nights for me. Now that the CEO had left, the questions that continued to haunt me were: Had I done everything I could? What was going on inside me, as I struggled with these forces? How was I handling the unraveling of a company I had supported for so many years? How was I coping with the deep disappointment of a very good friend and a threat to a friendship I cherished?

As I was wrestling with these challenges, my friend Bob Quinn, Professor at the University of Michigan Ross School of Business, posted a brief article in his blog entitled “An Elusive Leadership Skill.” [1] It prompted, in me, a cascade of ideas and reflections about leadership, all centered on the issue of coping with uncertainty in situations as complex as the one I was facing. I found two phrases in Bob’s post particularly thought-provoking:

  • Leaders “pursue their purpose by stepping into the crucible of anxiety,” and
  • Leaders “communicate the simplicity from the other side of complexity.”

The first phrase introduces the very descriptive and appropriate metaphor of a crucible: a container that can withstand severe conditions, usually high temperatures, which is often employed to conduct chemical reactions under harsh conditions. As I consider some of the most difficult leadership situations I have dealt with, many of which have involved personnel issues, I can picture stepping into such a crucible and standing there with a great “churn” in the pit of my stomach – and the sensation of being overwhelmed and even torn apart by the process.

The second phrase is derived from the wisdom of the early 20th century jurist Oliver Wendell Holmes who, in essence, said that he cares little about the simplicity on this side of complexity, but gives much value to the simplicity found on the other side of complexity. He is actually reported to have said it even more dramatically: “I wouldn’t give a fig for the simplicity on this side of complexity; I would give my right arm for the simplicity on the far side of complexity.”

Bob’s post could not have come at a more appropriate time, as it so aptly characterized my state of mind at that moment. I knew I had to remain immersed in the crucible. If I were to act without my full emotional engagement and instead simply ponder the elements of the situation dispassionately, I would be making decisions from the simplicity on this side of complexity — comfortable but irresponsible. I could also, at that point, have just resigned from the Board and left the issue behind — in effect, finding the simplicity for me, without much further regard for the complexity with which the company was dealing.

This put into focus a harsh reality of life: If we are to be players in an important mission, we have to endure the churn of the crucible and hope a new understanding crystalizes – or not step into it at all. There is no halfway measure: Full exposure is needed to appreciate the totality of a problem and do justice to our commitments with integrity and honor.

Full immersion is, of course, the lot of the CEO. It comes with the office. As members of the Board, our immersion should be no less intense, but we are granted a different vantage point and perspective, whence comes the value of our role. But just like a CEO, we need to be willing to absorb the anxiety of immersion and thus be open to learning in real time. And, perhaps most importantly, we must be able to overcome two elements that may easily mislead us: our egos and our prejudices. In the heat of the chemical reaction, we may not even notice these reactive agents.

In this situation, my ego pestered me to find a solution in short order, consistent with my image of being a seasoned executive. Meanwhile, my “better nature” struggled to find a path that would allow us to resolve the situation without damaging the dignity of the key players, in particular the CEO. As I pondered these issues, and at moments felt the natural urge to “escape the situation,” something became clear through the insights of Bob Quinn’s post: While we are compelled to dwell in the cauldron of uncertainty, our equally important task is to find a way to get to the other side of the combustion so that we can discern the essence of the quandary and gain clarity. We need to find the simplicity on the other side of the complexity. Yet it also became clear to me that while I needed to step out of the furnace, I had to do it without detachment. I still owned the situation! I had to maintain my link to the complexity but not be overwhelmed by it. I was not just an observer; I continued to be a protagonist. The admonitions that some were giving me to “be objective” or “be professional” totally missed the point.

No. I was not going to quit the Board. The only viable alternative for me was to fully continue in the complexity: to continue to be totally immersed in the subsequent deluge of facts and unknowns, of pressures and opinions, of perceptions and vested interests, and of major disappointments.

Converting the Crucible

When, in the heat of the Board deliberations, I suggested elevating the CEO to Chair I took a chance. I had not talked to the sitting Chair who had led the Board well for a long time. The Board was about to commit to a decision, there was no time for procrastinate. Many alternatives where considered; none of them sat well with me. I could have let the direction of the discussion continue and “go with the flow.” But I deeply felt the “rightness” of my approach, and had a deep, irresistible urge to express it. I was in what Bob Quinn calls “the state of authentic engagement.”[2] I spoke forcefully. It resonated with the other Board members. And I became the purveyor of the difficult news.

As I walked out of the Board room to fulfill my task one of the Board members, who is not known to be very “touchy feely,” turned to me and said: “Ric, I love you.” I do not believe he was talking about me per-se. He was talking about me as the carrier of the sense of the group at that moment. It was the leadership moment. It transcended me, it responded to the spoken and unspoken needs of everyone. I was just a conduit.

Many individual meetings followed. I was engaged, yet my head and heart were not totally clear. I was deeply immersed in the cauldron and feeling the constant heat of the reaction. I had trouble sleeping. At times, I was unable to think clearly. I was suffering. And it was compounded by the fact that the CEO then left and we were facing the disappointing clinical results. Something needed to change within me, if I was to continue to be a positive contributor to the company.

The change occurred one morning, several weeks later and deeply influenced by my reflections regarding the crucible of anxiety: In my daily meditation, I suddenly moved the crucible from the interior of my gut to just in front of me. While this sounds illusory, it was very real to me. In a moment of incredible clarity, I was able to “see” all the elements churning in the crucible of anxiety in sharp focus, and actual shift them out of my tense interior.

My early morning meditation ritual is a very spiritual time. Everyday, I take twenty minutes of very private time to sit still, quiet my mind, and attempt to move beyond the noises and pressures that crowd my thinking and my psyche (including those that are conspiring to tighten my gut.) Once in a while, this practice allows me to reach a state of deep peace, which carries with it an empathy and caring for everything and everyone, near and far. That is just what I needed, in the current state of affairs, and suddenly, instead of a crucible, I found myself holding a different sort of receptacle in my arms, which contained all the churning elements. But it was now in front of me where I could see it, rather than ominously lurking inside me. Importantly, this vessel felt amicable, not antagonistic. I felt love (yes, love) pouring into it, and a strange new ability to attend to each part of the mix – people and situations – in a warm and caring way. This experience startled me: I had converted the crucible of anxiety into a chalice of change.

The moment was unbelievably liberating. My ego dissolved and I became focused only on the highest good. My purpose as a member of the Board clarified and became not just another job, but a sacred task. My fear turned into confidence, and the chalice enabled me to finally employ all of my leadership tools more effectively: my analytical capabilities, my sense of purpose and passion, my moral compass and my spiritual anchors. This would not have occurred had I not been practicing my daily mediation.

I use the word “chalice” advisedly. The crucible burns with intolerant heat, while the chalice refreshes and rejuvenates, bringing transformation when we drink from it. To me, the chalice connotes a vessel that purifies, transmuting the elements and giving us an ability to see the process with greater clarity.

The moment I embraced the chalice I was transformed. I had a much firmer view of the dynamic whole, and sensed the simplicity on the other side of complexity. Most importantly, I found the strength to be fully present while confronting the conflicts with gentleness. I recognized the best in each actor, and I felt that no matter what I had to do, I could perform my duties with respect for each party. And part of that feeling of compassion was toward myself.

This came as the Board made the wrenching decision to liquidate the company. Several of the other Board members chose to leave. I chose to continue. The chalice transformation made it clear to me that I had to see the situation through to the finish, regardless how painful it was to disassemble a company with which I had been associated for a dozen years. My goal, together with two other Board members, was to implement the wind-down in a manner that safeguarded the dignity of the employees who had worked so tirelessly in the pursuit of our dream of a medical breakthrough and, equally important, to find a home for the technology that would ensure the continued pursuit of the possibilities of a treatment that might save the lives of our children and grandchildren. I also dedicated myself to rebuilding my friendship with the CEO, which had been deeply frayed by the events that had unfolded. I could not have done this had I not converted the crucible into a chalice.

A Crucial Conversion Ingredient

I believe that this flow through complexity to simplicity has deep spiritual significance. It is therefore not surprising that the insight of the conversion from crucible to chalice came to me during meditation. It also indicates that there is a much deeper aspect of this that could have implications for our leadership – and life – journeys: our ability to hold opposites without feeling threatened.

A special passage from Father Richard Rohr’s book Eager to Love keeps coming back to me in this context[3]:

Paradox held and overcome is the beginning of training in non-dual thinking or contemplation, as opposed to paradox denied, which forces us to choose only one part of any mysterious truth. Such a choice will be false because we usually choose the one that serves our small purposes.”

This suggests that avoiding our “smaller purposes” becomes crucial when we need to transform the crucible to a chalice. This is also true when we face many of our leadership challenges. In my classes and in my book, I speak of the necessity for leaders to continuously move from the specific to the general, from the narrow to the broad. As leaders, we absorb the broad uncertainty of our venture so that others on the team can focus on more specific aspects of the mission, which they are often much more qualified to tackle. I liken this to our breath: When we breathe in, we expand our horizon, taking in the 360-degree vista. We are alert to opportunities and threats without blocking them with our prejudices and small purposes. Yet we cannot just breathe in; to survive we must also breathe out. When we do, we transmit energy, passion, direction and focus. It is a continuous flow. In the breathing-in phase, we must hold opposites. We need to be able to encompass paradox. We need the capacity to fully entertain conflicting positions. And we need to fully understand contrasting positions from those who advise us.

The Leadership Voice

To sense the “simplicity on the other side of complexity” is not enough. Our task is to permit our leadership capacity to manifest. We must therefore unshackle it. The transformation from crucible to chalice is a step in this “coming out” effort. I propose that true leadership springs from an inner well that sustains an inner flame. It is a delicate flame, protected by a lifetime of defense mechanisms that develop as we cope with our personal experience of living. To allow an opening in this armor without damaging the inner layers is subtle and delicate, yet that is the required effort.

The place that I am talking about is difficult to describe. A wonderful passage from Thomas Merton perhaps does so best[4].

“Again, that expression, le point vierge, comes in here. At the center of our being is a point of nothingness which is untouched by sin and illusion, a point of pure truth, a point or spark which belongs entirely to God, which is never at our disposal, from which God disposes of our lives, which is inaccessible to the fantasies of our own mind or the brutalities of our own will. This little point of nothingness and of absolute poverty is the pure glory of God written in us, as our poverty, as our indigence, as our sonship. It is like a pure diamond blazing with the invisible light of heaven. It is in everybody, and if we could see it, we would see these billions of points of light coming together in the face and blaze of a sun that makes all darkness and cruelty of life vanish completely. I have no program for this seeing. It is only given. But the gate of heaven is everywhere.”

And, of course, the beauty in this is that as our leadership voice springs from a point of light linked to all lights, it speaks directly to the light in other individuals. They feel it. They do not have to go through the intellect to sense it fully: It is expressed from that deeper place. It prompts even the hardest of us to say, “I love you.”

An Opportunity for Reflection and Deep Learning

Bob Quinn, in his book Deep Change: Discovering the Leader Within,[5] looks at leadership not as behaviors and techniques, but as a “state of being.” As a guide and teacher, I echo Bob’s thoughts. The capacity for leadership is in all of us. As Bob’s book title suggests, we just have to discover it.

The challenge for us as teachers is to figure out how we can help others (and ourselves) with this discovery; what we can do to “free” ourselves to capture that capacity; what state of mind allows us to manifest it in the right moment. How do we train for it? How do we coach it?

Two words in Father Rohr’s quote are noteworthy, as he refers to paradox: “held” and “denied.” What are we constantly denying as we face situations? What makes us deny? Does therein lie the secret ingredient — the catalyst for a crucible to chalice transformation? How do we train to hold paradox?

Here are some recommended steps for making the most of the opportunity when we come face-to-face with uncertainty:

  • Recognize the complexity.
  • Know that our job as leader is to fully enter the crucible of anxiety.
  • Acknowledge that it will be uncomfortable.
  • Commit to remain in the crucible as long as you need to, resisting the temptations of “easy” solutions.
  • Allow the transformation of the crucible into a chalice (by the deep reflection and contemplation that allows a mindset change and converts the problem into a sacred task rather than a burden) thereby gaining the peace that enables the discernment needed to help you arrive at the eventual decision or action.
  • Then, step to the other side of complexity with the simplicity offered by clarity.
  • Act only when you have reached the simplicity on the other side of the complexity.
  • Enact your decision with conviction, confidence and respect. Capture the leadership moment. Speak from your “center.”

Consider the times when you have felt the crucible emerge. Were you able to transform it into a chalice, even if you may not have characterized it as such at the time? What did you learn from this? Examine how you might improve such situations and how, in the future, this might help you in better leading your organizations or teams.

And perhaps even more broadly: Might the crucible-to-chalice model help you in resolving your own personal affairs?


[1] https://thepositiveorganization.wordpress.com/2016/07/20/an-elusive-leadership-skill/

[2] Bob Quinn Post June 24, 2016

[3] Richard Rohr, Eager to Love: The Alternative Way of Francis of Assisi ( Cincinnati, OH: Franciscan Media, 2014)

[4] From Merton’s Conjectures of a Guilty Bystander, quoted in Lawrence S Cunningham, Thomas Merton: Spiritual Master, Essential Writings (Mahwah, NJ: Paulist Press 1992) p 146

[5] Robert E Quinn Deep Change: Discover the Leader Within (San Francisco: Jossey-Bass 1996


Dear Reader:

I write my blogs sporadically. Triggered by particular events or situations with which I am deeply involved, I find myself prompted to write because of the acute nature of the matter. This post, however, is different. The subject has been lingering inside me for a long time. It rarely rises to the acute level, but rather I feel it as a dull “chronic” discomfort in situations when I sense a problem, but the stimulus is not strong enough to incite me to act. And then I bemoan the fact that I did not act in time. It’s like an ache telling me I should go and see the doctor… Yet I don’t go, figuring that trying to describe it would be too amorphous and thus embarrassing. Of course most of the time, it dissipates and life goes on just fine. But sometimes it does not.

The subject? Maximizing the effectiveness of a Board of Directors. I have been involved with Boards for almost half a century, and I attribute much of my entrepreneurial success to the extraordinary nature of the Boards I have been privileged to build and serve under as CEO. As I reflect on what worked so well, a few factors are evident:

  1. Each member of my Boards has been a superb professional.
  2. Members have joined my Boards because they believed in the company mission and trusted the executives.
  3. They did not do it for money, yet felt respectfully compensated for their efforts.
  4. They respected the other Board members, enjoyed their company, and did not hesitate to express their opinions while listening to the opinions and positions of their colleagues.

At the same time, I recognize that the Board of Directors is often comprised of strange bedfellows, which can be awkward. Meetings are few and far between, often months apart; some of these meetings are by phone; in-person meetings are even more infrequent. Members may know each other outside of the Board, but most likely do not see each other very often. They may live in different parts of the country or the world. To say they are a team is sometimes a stretch. To make them a team is possible but takes concerted effort. Yet Board members have a weighty responsibility: to monitor the company’s performance on behalf of the shareholders and ensure that execution meets expectations. To do so, one of their most important responsibilities is to hire and monitor the performance of the CEO. Yet for their deliberations and decisions, they depend on information that is provided by the CEO – who is, most likely, also a member of the Board. This places the CEO in a strange position: being a part of a group from which he or she may be excluded, when certain decisions are taken behind closed doors.

Most of the time this works very well. In addition to the caliber of the Board members, two critical factors facilitate good results:

  1. An active effort on the part of the CEO to work with the Board, by communicating often, managing the information flow and making key executives available for complementary discussions; and
  2. The skill, sensitivity and impact of the Board Chair.

It is the Chair on whom I want to focus in this article. I have been privileged to act as Chair on many Boards, as well as to serve as a Board member under many different Chairs. As I think back to the most critical growth periods of my companies, I attribute part of our success to my discipline in taking time to check in on all Board members frequently, to keep the information flow current, to never allow for any surprises, and to ensure that views are expressed and heard even in the most pressured moments. The times when I did not do well as Chair occurred when I fell into a few traps, which I describe below as typical “Syndromes.”

While many shortcomings can manifest themselves during the normal course of Board business, many manifest during Board meetings. The challenge is that Board meetings can be highly “charged” by the very nature of the participants, their inherent intensity and the import of their role. To work best, Board meetings require members – in particular the Chair – to be very aware of and present to emerging dynamics. When the tenor begins to crescendo, a good Chair senses this and redirects the energy before a discharge occurs. If, on the other hand, the Chair is affected, in whole or in part, by any of the Syndromes outlined below, things may rapidly take a course that is unanticipated or unintended.

The “Strongest Voice” Syndrome

A situation that appears in particular at Board meetings is something that all Chairs face: the Board member with the strong voice and the quick mind (especially financial), who can overwhelm a meeting and reduce the opportunity for considered deliberation, often by dint of his or her brilliance and eloquence. In doing so, such a strong voice may rob the Board of the great value of hearing different viewpoints and shared experiences. I learned this the hard way with some very vocal Board members in the early years of my entrepreneurial journey. But I also learned that if managed properly, such a situation can end with very positive results. One case that is strikingly vivid in my mind was when my young and small pharmaceutical company considered buying a large manufacturing plant in North Carolina. It contained a very sophisticated sterile manufacturing facility, something that was outside of our expertise. One Board member stated flat out that such a move would be crazy. His voice seemed particularly relevant because the facility had been built under his watch when he was CEO of the seller, a large drug company. You can imagine the weight of such an opinion. Fortunately, we were able to navigate the discussion to an examination of what it would take to make such an acquisition possible and prudent (in addition to the need for sizable funding which, at that point, we did not have.) In the end – and that end was 10 months later – we did make the acquisition and it catapulted our firm to be the largest outsourcing manufacturer of drugs in the Americas.

The “Founder” Syndrome

Being a company Founder is one of the greatest joys of the entrepreneur, especially if the enterprise grows. As I advise many Founders, a critical part of success (as it certainly was for me) is building superb Boards. Ideally, the Board is truly a strong, independent voice that enriches the leadership, guides and mentors the entrepreneur, and ensures that the business avoids mistakes that waste time and money. For this to be the case, an active, free and candid dialogue at the Board level is paramount. We must be careful not to overwhelm the Board with our “Founder’s aura,” which can be limiting. We tend to be so focused on our passionate vision that our capacity to listen may be affected. Selective hearing is a common ailment. We Founders need to constantly remind ourselves to clear our ear canals.

The “I am Still the Boss” Syndrome

This happened to me several times, and is related to the Founder-Chair issue described above. I founded a company of which I was CEO for many years. Eventually, I transitioned to Chair when we brought in a new CEO more capable of further growing the company. My shortcoming as Chair was due to the presence, often inadvertent, of my fingerprints on the everyday running of the business. I had given up the CEO title, but never fully let go. And the new CEO could feel it, as could the employees. Without meaning to, I was exerting an influence over the company that did not allow the new CEO to fully gain the leadership needed to propel the company to new levels. And I never appreciated that because of my lingering presence the incoming CEO – who I had recruited and felt very positive about – never entered the full covenant needed for him to be an effective entrepreneurial leader. A few years later, he found “a better offer” and resigned, giving us a very “generous” three-week notice. When I asked him how he could leave the company hanging at such a critical time, he simply said, “Well, what’s the problem? You’re still here.” That told the whole story.

The “Confusion between Executive and Non-Executive Chair” Syndrome

There are circumstances when companies need to have an Executive Chair as well as a CEO. This might occur during a transition period when a President is promoted to CEO or when a new leader is transitioned into the company from outside. In general, the Executive Chair holds some of the responsibilities of the CEO, and spends much more time on the company’s business than an ordinary Chair would or should do. The responsibilities of the Executive Chair often include some operations, whereas a non-executive Chair’s do not. The problem occurs when a Chair acts as if he or she is Executive Chair – often without even noticing it. In the process, the Chair will disenfranchise the CEO, eroding some of the CEO’s initiative, and not allow the CEO to fully become the organization’s leader. This is a very inefficient situation. While I may have good intuition and the best intentions, as Chair I may suggest initiatives to the CEO. Only when such initiatives are wholly “owned” by the CEO do they stand a chance of being successfully implemented. Implementation is not our job as Chair, although our demeanor may raise expectations to the contrary.

The “Clinical” Syndrome

As Chair, we are tasked with many key activities on behalf of the Board. They include being the key interface between the Company and the CEO in negotiating the employment agreement, coordinating performance assessments, reviewing compensation, or the much more difficult task of negotiating the exit of a CEO who is being replaced. As with so many complex negotiations, personal feelings may make the task more difficult. In those situations, some of us tend to take a more clinical approach and keep it impersonal. This may work well to get the best “terms” but, in the end, is not likely to yield a win-win outcome. Hiring, performance reviews and the rare need for separation are very sensitive and personal events for all involved. Showing the warmth of our humanity in these times is essential for a good outcome. As Chair, we need to remember this. Yes, we represent the Board, which is a somewhat impersonal “body,” yet it is an entity comprised of individuals. Part of our task is to carry this humanity to the discussion, regardless of whether being “detached” might seem the more expedient approach.

The “Overbearing” Syndrome

Let’s face it: Those of us in CEO or Chair positions are, by definition, individuals with strong personalities and, often, high adrenaline levels. We are passionate about what we are doing, and approach every task with gusto and exuberance. As we grow in our leadership journey one of our most important learnings is how to “tune” this enormous energy to be appropriate for different situations. Some of us are not very aware of the “long shadow” our personas cast. Sometimes, our hugs (while meant with a genuine and caring intent) can be too tight. I have both embodied this myself and seen it in others. The challenge is how to be fully present to this dynamic, especially in the Chair-to-CEO relationship. If our inclination is to get too involved, we need to recognize when we are stealing some of the breathing space from our CEO, and pull back.


The net of this post: If you are Chair, take the time to examine whether there are any aspects of these syndromes that ail you. If the answer is “Yes,” talk to fellow Board members or the CEO about your concerns, and recruit these colleagues to monitor you and help you become a better Chair. Further, I propose that neither the Chair nor the CEO are the most effective monitors of their own performance – or for that matter of the Board as a whole. These are tasks best relegated to a skilled external resource whose objectivity and professionalism inform their insights. So consider engaging an outsider for a regular 360 review of your performance as Chair and the effectiveness of your Board. While this may be time consuming and add expense, it is an extremely valuable investment that can make the difference between a good Board and an excellent Board. I have found such 360 reviews by an outside professional to offer some of my own best opportunities for personal growth. It also does wonders in “lubricating” the dialogue among Board members.



As I write this, two popular sayings come to mind: “Time flies when you’re having fun,” and “The best way to learn is to teach.” The five years since the publication of my first edition of Letters to a Young Entrepreneur have flown by. It certainly does not feel that long! Perhaps this is because after the book came out I entered a new wonderful phase in my life: I became a teacher.

Four years ago, the Chair of the Chemical Engineering Department at Stanford University, Eric Shaqfeh, asked me to teach a course on entrepreneurship, focused on the Engineering and Science industries that his graduates would be considering for their careers. To overcome my initial hesitation, Eric suggested I co-create the course with Howie Rosen, a fellow Stanford Chemical Engineering graduate. Howie had been involved in several biotech start-ups and became President of Alza Corporation shortly before it was acquired by Johnson & Johnson. He had already been teaching a number of biotech courses in the Engineering and Business School and was very familiar with the Stanford academic operation. This presented a wonderful opportunity for me to share my experience and convert the concepts I had presented in Letters into lectures and discussion material for seniors and graduate students interested in understanding the making of an entrepreneur.

In the process of shaping the course, I more keenly realized how the entrepreneurial leadership concepts in Letters apply to all of life—whether we are engaged in growing a small business or a large company, or in some other vocation that requires building and leading teams. After several years of teaching the course, I found that many new ideas had sprung from the students’ questions and challenges. I therefore decided to substantially expand Letters to provide my students with a more comprehensive basis for our dialogue. The increased scope of the second edition prompted me to add a sub-title reflecting that greater breath: Succeeding in Business Without Losing at Life — A Leader’s Ongoing Journey.

The new book is available from Amazon and other outlets, and will soon be available in electronic form on Kindle and iBooks. Convenient links to order the book can be found on this website.

I thank you all for your continued friendship and support.



Over the last several years, while working with my students, I have developed a series of descriptors that profile the entrepreneur. They are based on my experience as a life-long creator of new ventures. Like all “lists,” this is an abbreviated articulation of what is a complex and multi-faceted whole. Yet it serves to highlight some elements of what all entrepreneurs need to consider, as we strive to become better leaders.

My list is split into three domains of the entrepreneurial character: Inner, Outer and Core. I am not attempting to be comprehensive; I mainly want to trigger an active conversation that deepens our understanding of what makes an entrepreneur. Here is the short list:

INNER: -Passionate -Positive -Risk Tolerant -Big Thinker -Visionary
OUTER: -Articulate -Clear -Enthusiastic -Inspiring -Nimble
CORE: -Consistent -Authentic -Persevering -Discerning -Grounded

Clearly, many other characteristics might be added. Here are a few that have been suggested in my class discussions: Salvager (I like this one!), Dreamer, Realist, Courageous, Charismatic, Tough, Resilient, Self-confident, Good Self-esteem, Integrity. I am sure that you can think of others, and I welcome any ideas. My main aim is to take these characteristics and examine what I call the three key habits that an entrepreneur needs to master if he or she is to become a good leader: To Balance, To Breathe and To Trust.


This may seem to be the easiest of the three, but yet is so often forgotten. The main reasons we entrepreneurs tend to neglect balance are:

1. We do not know ourselves well enough to identify our strengths and shortcomings (or if we do, we are unable to admit them, which amounts to the same thing), and

2. We are impatient. Often, for us, it is so much easier to just plow ahead, figuring that by the time we tell others what we want to do and how we want it done, we might as well do it ourselves. Yet the key to growing a venture is to engage others in the journey, and then deploy all constituents in the optimal way to reach our goal. To do this, we need to find balance, starting with ourselves.

Let’s take another look at the list of domains above, and consider where we sit in the optimist-realist scale. When I ask my students, most identify themselves as optimists. While that is fine (since a non-optimistic entrepreneur will find it hard to gain a following), we have to be very careful not to overlook the criticality of realists in our midst. In my book Letters to a Young Entrepreneur, I mention a number of instances in which having hard realists around me balanced my rose-colored glasses and saved our company.

Perhaps of more immediate relevance to all of us is the balance between leading and managing. For most of my entrepreneurial career, I never really tackled that question. I just did what I thought needed to be done, often resulting in micromanagement, and thus often limiting the creativity and contribution of others. Later, as an “entrepreneur emeritus” and teacher, my course preparation led me to a classic Harvard paper on the subject: John P. Kotter, What Leaders Really Do, HBR December 2001. I urge you to read it. It captures, in a wonderful way, a vital topic. I summarize Mr. Kotter’s concepts as follows:

Where a leader points, a manager plans.
Where a leader aligns, a manager organizes.
Where a leader inspires, a manager problem-solves.
Where a leader produces change, a manager produces predictability.

What each of us should examine is our propensity to lead or to manage. There is no value judgment in this question. Both are essential. The key lies in matching our skill with the need: achieving balance!


As we grow in responsibility, whether in our own entrepreneurial ventures or in our roles within larger organizations, we expand the breadth of the topics that fall within our purview. We gain an increasingly broad sense of the task at hand, and we take on an increasing span of responsibility and accountability. In Letters, I introduce the concept that a leader’s main job is to absorb uncertainty (Chapter 3.) Presumably, as leaders by definition we have a more comprehensive view of the venture than do others – or at least we should have. Think of what we do when we drive a car: as we approach a sharp curve, our eye is (or should be) ahead of the curve. This makes for better and smoother steering. Also, as we “see” more of the road, we feel more secure in our steering. In the concept of “absorbing uncertainty,” a leader takes on the larger burden, so that others on the team can focus on more defined parts of the task.

To do the leadership job right, we need to encompass as much of the “scenery” as possible. I equate this with taking a deeper breath, as we spread our arms (and our awareness) to a broader horizon. This also requires us to look to the very edges of our field of vision – for threats and opportunities that may be less obvious.

This is the breathing in part.

However, we also need to breathe out, exhaling our breath in a purposeful manner to help our team gain focus and direction. As we breathe out, we point the way.

And this is the toughest part, at least for me: we need to breathe in and breathe out, continuously. My tendency is to dwell in one mode or the other – spending too much time either scanning the horizon or burrowing toward the completion of a particular project. To keep our venture healthy and alive, as leaders, we must sustain a constant flow between the two: breathing in and breathing out.


Both in breathing in to absorb uncertainty and breathing out to provide focus, a key ingredient is the mutual trust between our venture companions and ourselves. That requires us to be vulnerable, so that people can truly feel the genuineness of our commitment. And it requires that others “surrender” their reservations and have faith. That faith is critical. Without it, what we do is just mechanical and lacks the directional vector — the deeper purpose that is so important in providing energy to move toward our goals, whether we are leading or following. In Letters, I speak of trust packets as the vehicles in the exchange of commitments between leader and team member. I also speak of commitment as a mutual covenant, not policed by an outside document or a quality control officer. It is an internal act, upheld only and solely by our inner character.

This trust factor is the essence of the core within each of us. It raises the very fundamental question: can one learn to trust? Look at the adjectives I chose for the Core group above: Consistent, Authentic, Discerning, Persevering, Grounded. Are these innate? Or can they be trained?

The reason that this is an important issue in my course is my desire to leave my students with the tools to expand their leadership capacity. So I ask them to examine all the characteristics outlined at the beginning of this article (Inner, Outer, Core), in terms of whether they are shareable, learnable or innate — a topic of very rich and important dialogue, which touches on all three of the vital habits considered in this article: Balance, Breathing and Trust.

In all of these discussions with my students, something has bothered me: the prevalence of the designation “innate.” It implies that we either have “it” or we do not. It implies finality. Core is, by its nature, deeply internal — you cannot have others “cover for you.” If you do not have it, you are “done-in.”

I have begun to take a different view. I have come to believe that everyone of us has the capacity for integrity, honesty and authenticity. Each of us has a deeply seated spark of goodness. But as we fend off the challenges of living, we tend to develop coping mechanisms that “shield” this spark of light. We grow a “shell” around our spark — a shell of varying thickness, depending on our own personal life journey. Our task in learning to be good leaders and, for that matter, happy people, is to learn to shed — or at least crack — this shell, so that the inner spark can shine through. As others see our light, it becomes easier for them to trust us to lead our entrepreneurial ventures to success.